Vat dyestuffs of anthracene series containing nitrogen and process of preparing same



Patented May 20,-

' UNIT-El) STATES nan mm: m Josarsrocx, or HOCEST-OlI-THE-EAIN, seam, assreuons To "C. to 275 (3. (produced by re va'r ms or ms con'rm'mo in'rnoeim Y ranranme sum ju rnoon'ss or PA ENT omen m WORKS, INC O F NEW YORK, N. Y.,' A COBBOBATION 0F DELA- e aonmv n Application filed June 31,. was, Serial no. 117,588, and n Germany 1..., a, 19:5.

Our present invention relates'to the preparation of vat dyestufis containing nitrogen. I By the action'of nitrating agents upon a Bz-l-halogenbenzanthrone there are obtained nitrohalogenbenzanthrones containing the nitro group in the I the benzanthrone which isdproved by'the fact that when they aredegra ated'by oxidation a'ci 4 Nowwe have found that aminohalogenbenzanthrones, obtainable from the'above mentioned nitro products are not substituted in the 2-position and therefore can be condensed-by melting themvwith alkaline condensing agents and; that in this way valuable vat dyestufis are obtained. They are di- .benzanthronederivatives containing nitrogen which differ from the roducts which are obtained if a previously ormed 'dib'enzanthrone .or iso-dibenzanthrone (compare U. S. Pat-' and then reduced. I

The vat dyestufis'which can be prepared .b our new process are ofparticular' commercl al value owing to the remarkable tint they ents Nos. 796,393 and 1,063,000) is nitrated ve.- The followin examples serve toillustrate our invention, ut are not intended to limit itthereto: i r A 1. 10 partsby weight of'aminobromobenzanthrone which has itsmelting; point at 274 ucing nitroobenzanthrone of melting. point B z-l-bro into caustic alkali and 7 5 parts of alcohol and the resulting molten mass iskept at 140 C. to 150.,O.. 'for"% hours. The mass is then poured into water, .and by" blowing air into it the 'leuco compound, bein in solution,is precipitated and afterwar washed.- The dyestufi thus obtained forms a dark colored paste and, when dry, an almost black powder which dissolves in con- .centrated sulfuric 'acid with a brown color of a violet hue. It dyes cotton from a bluishviolet vat directly reddish y to'black tints which, I hen treated c lorine, assume a green hue.

theyield mtroanthraquinone-l-carboxylic I 2. As. new

' .filtered and Analysis of the crude dyestufl shows a nitrogen content 01Ev 4.25 percent, i.e., a-vfalue which approaches the theoretical amount of nitrogen (5.76 per cent) calculated for a 'diaminodibenza'nthrone. anthraquinone residue of Contrarythereto the nitrated violanthrone produced by the process described S.

Patent No. 793,393 yields, as isknown, green 'dyeings on cotton which, on bein'g chlorinated, change to a color varying from 'grey to black, whereas nitratediisoviolanthr'onm '(SQO U. S. Patent No. 1,063,000) gives-on cotton greenish-blue'tints.:

2. If for the bromaminobenzanthrone used according to Example 1 is substituted the am no-Bzel-chlorobenzanthronewhich has its melting point alt-290 C. to 291 C. (obtained from Bz-1-chloronitrohenzanthrone of melt- .j--. mgpoint 284 C. to 285 C.), a dyestufi posf70 I is obtained- The fact that the dyestu -'-gives-' almost thesame tinctorial pro l'tlQS a green solution'in concentrated sulfuric-acid, proves that the product obtained according to the present example constitutes chemically a urer isodibenzanthronederivative. .eclaim: 1 Process of the anthracene series containing nitrogen which consists. in treating with caustic alkalian amino-Bz-1-halogenbenzanthrone compound, produced by acting with anitratobtained.

anthracene series containing nitrogen which are in a dry state almostblack powders, dye

cotton from a bluish violet vat directly reddish gray to black tints which'when treated with chlorine assume agreen hue, dissolve in concentrated sulfuric/T acid with figbl'OWll to roducts vat dyestuffs of the I for preparing new vat dyestu'flfs- 1ng agent upon a Bz-l-halbgen-benzanthrone jand reducing the nitrated compound thus green color, and are obtainable by treating .withcaiistic alkalithe amino-Bz-l-halogem benzanthrone comunds produced by acting with nitrating age upon a Bz-l-halogem benzanthrone and reducing the nitrated-com-' I pound thus obtained.

3. The process for preparing new vat dyestufis of the series containing mar e I which treatingwith caustic alkali the amino-B2-l-bromo-benzanthrone, having the melting point 274 C. to 275 (1., produced by acting with a nitrating agent upon Bz-1-bromo-benzanthrone and reducing the nitrated compound having the melting point 290 (1., thus obtained.

4. The process for preparing vat dyestuffs of the anthracene series containing nitrogen which consists in treating with caustic alkali in the presence of alcohol at a temperature of 140 C. to 150 C. an amino- Bz-l-halogenbenzanthrone compound, produced by acting with a nitrating agent upon a Bz-l-halogenbenzanthrone and reducing the nitrated compound thus obtained.

5. The process for preparing vat dyestuffs of the anthracene series containing nitrogen which consists in treating with caustic alkali in the presence of alcohol at a temperature of 140 C. to 150 C. an amino-Bz-l-bromobenzanthrone compound,.having the melting point 274 C. to 27 5 C.,'produced by acting with a nitrating' agent upon a Bz-l-bromobenzanthrone and reducing the nitrated compound having the melting point 290 C. thus obtained.

6. As a new product a vat dyestufl' of the anthracene series containing nitrogen which is in a'dry state an alinost black powder, dyes cotton from a bluish violet vat directly reddish gray to black tints which when treated with chlorine assume a weak green hue, di's solves in concentrated sulfuric acid to a brown solution with a violet hue, and can he obtained by treating with caustic alkali the amino-Bz-l-bromo-benzanthrone. having the melting point 274 C. to 275 C., produced by acting with a nitrating agent upon Bz-l-bromo-benzanthrone and reducing the nitrated compound having the melting point 290 0., thus obtained. In testimony whereof, We aflix our signatures.

KARL WILKE. JOSEF STOCK.

CERTIFICATE or CORRECTION.

Patent No. 1, 759, 249. G t ym 20; 93

KARLIWILKE ET AL.

It is hereby certified that error appears in the printed specification of the above numbered patent requiring correction as follows: Page 1, line 58, for Y Y "793,393" read "796,393"; and that the said Letters Patent shouldrrbe read with this correction therein that the same may conform to the record of the case in the Patent Office.

Signed and sealed'this 22nd day of July', A; n. 1930;

Wm. A. Kinna (Seal) Acting Commissioner of Patents. I 

